Propylamine → HCID 178457563, compound

HRID 2398334Notes

Reaction equation

HRID 2398334 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])SC)#[N:2].[CH2:18]([NH2:21])[CH2:19][CH3:20]>C(O)C>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])=[N:21][CH2:18][CH2:19][CH3:20])#[N:2]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 178503877HCID 178503877, compound

Product 1

HCID 178457563HCID 178457563, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-S-methylisothiourea (2.69 g.) and n-propylamine (1.1 g.) in ethanol (50 ml.) was heated under reflux for 6 hours. Concentration, followed by chromatographic purification on a column of silica gel with ethyl acetate-isopropyl alcohol (4:1) as eluant and final recrystallisation from aqueous isopropyl alcohol afforded N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-propylguanidine (2.0 g.) m.p. 108°-110°. (Found: C, 51.4; N, 7.4; N, 30.0; S, 11.4. C12H20N6S requires: C, 51.4; H, 7.2; N, 30.0; S, 11.4).

Workup

  1. temperatureunder reflux for 6 hours
  2. concentrationConcentration
  3. customfollowed by chromatographic purification on a column of silica gel with ethyl acetate-isopropyl alcohol (4:1) as eluant
  4. customfinal recrystallisation from aqueous isopropyl alcohol

Sources & evidence

ORD record
ord-07b033a181ba4209b499b36c67450180
Source dataset
uspto-grants-1977_05
Patent number
US04024271

Reaction notes

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